Urbanization is believed to result in a transition towards energy-dense diets, sedentary lifestyles, and a subsequent increase in the burden of hypertension (HTN) and other cardiovascular diseases (CVDs) in developing countries. However, the extent to which this occurs is likely dependent on social contexts. We performed multilevel logistic regression models to examine whether the association between incident HTN and the degree to which a community exhibits urban features varied by region (the Northeast, East Coast, Central, and West) within China and period. We used longitudinal data from the China Health and Nutrition Survey (1991–2015) and stratified analyses by sex. Among women, the positive association between medium-to-high urbanicity and HTN onset generally shifted to negative between 1991 and 2015. The high urbanicity was associated with lower odds of developing HTN in the East Coast from the early 1990s. The negative association between high urbanicity and HTN occurrence became statistically significant during 1991–2015 in the Northeastern and Central Regions, while the association remained positive and non-significant in the West. Among men, the relationship between urbanicity and incident HTN was generally non-significant, except for the East Coast in which the negative association between high urbanicity and HTN occurrence became statistically-significant in more recent years. Our findings suggest that, when a subnational region or the society as a whole has become more economically developed, higher urbanicity might turn out to be a protective factor of cardiovascular health. Moreover, improvements made to communities’ urban features might be more effective in preventing HTN for women than for men.